5176-27-2 | t-Butyl 1H-pyrrole-1-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$12.00	$8.00
5g	95%	in stock	$13.00	$9.00
10g	95%	in stock	$17.00	$12.00
25g	95%	in stock	$23.00	$17.00
50g	95%	in stock	$30.00	$21.00
100g	95%	in stock	$59.00	$42.00
500g	95%	in stock	$279.00	$195.00

Description

• Catalog Number: AB43014
• Chemical Name: t-Butyl 1H-pyrrole-1-carboxylate
• CAS Number: 5176-27-2
• Molecular Formula: C9H13NO2
• Molecular Weight: 167.205
• MDL Number: MFCD00209559
• SMILES: O=C(n1cccc1)OC(C)(C)C

Computed Properties

• Complexity: 166
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• XLogP3: 1.9

Upstream Synthesis Route

The upstream synthesis route of t-Butyl 1H-pyrrole-1-carboxylate typically involves the following steps:

1. **Synthesis of Pyrrole**: The starting material, pyrrole, can be synthesized by Paal-Knorr synthesis, which involves the reaction of a 1,4-diketone (such as 2,5-hexanedione) with ammonium acetate to form pyrrole.

2. **Functionalization at the 1-Position**: The pyrrole undergoes lithiation using an organolithium reagent, such as n-butyllithium (n-BuLi), to form a pyrrolyl lithium species at the 1-position.

3. **Carboxylation**: The lithiated pyrrole is then treated with carbon dioxide (CO2) to introduce the carboxylate group, resulting in lithium 1H-pyrrole-1-carboxylate.

4. **Esterification**: The final step involves esterification of the carboxylate salt with t-butyl alcohol (t-BuOH) in the presence of a strong acid catalyst, for instance, sulfuric acid (H2SO4), to yield t-Butyl 1H-pyrrole-1-carboxylate.

Each step must be carefully controlled for temperature, time, and stoichiometry to ensure high yield and purity of the desired product. Inert atmosphere techniques, typically involving nitrogen or argon, are employed to prevent unwanted side reactions due to the sensitivity of pyrrole to oxidation.

Literature

• Ethynyl-linked (pyreno)pyrrole-naphthyridine and aniline-naphthyridine molecules as fluorescent sensors of guanine via multiple hydrogen bondings.

  The Journal of organic chemistry 20070105

• Synthesis and radiosynthesis of [(18)F]FPhEP, a novel alpha(4)beta(2)-selective, epibatidine-based antagonist for PET imaging of nicotinic acetylcholine receptors.

  Bioorganic & medicinal chemistry 20060601

• A noncarbohydrate based approach to polyhydroxylated pyrrolidizines: total syntheses of the natural products hyacinthacine A1 and 1-epiaustraline.

  The Journal of organic chemistry 20050902

• Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline and tripeptides containing them.

  The Journal of organic chemistry 20040625

• Enantiopure oxazolidinones as chiral acids in the asymmetric protonation of N-Boc pyrrole derived enolates.

  Chemical communications (Cambridge, England) 20040321